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25
Subjective

What will be the product obtained as a result of the following reaction and why?

Explanation

When Friedel-Craft alkylation is carried out with higher alkyl halide, e.g., $n$-propyl chloride, then the electrophile $n$-propyl carbocation ( $1^{\circ}$ carbocation) formed which rearranges to form more stable iso-propyl carbocation ( $2^{\circ}$ carbocation). Afterward the main product iso-propyl benzene will be formed.

26
Subjective

How will you convert benzene into (a) p-nitrobromobenzene (b) m-nitrobromobenzene

Explanation

Halogens attached to benzene ring is ortho and para directing where as nitro group is meta directing.

27
Subjective

Arrange the following set of compounds in the order of their decreasing relative reactivity with an electrophile. Give reason.

Explanation

The methoxy group $\left(-\mathrm{OCH}_3\right)$ is electron releasing group. It increases the electron density in benzene nucleus due to resonance effect (+ $R$-effect). Hence, it makes anisole more reactive than benzene towards electrophile.

In case of alkyl halides, halogens are moderately deactivating because of their strong $-I$ effect. Thus, overall electron density on benzene ring decreases. It makes further substitution difficult.

$-\mathrm{NO}_2$ group is electron withdrawing group. It decreases the electron density in benzene nucleus due to its strong - $R$ - effect and strong $-I$-effect. Hence, it makes nitrobenzene less reactive. Therefore, overall reactivity of these three compounds towards electrophiles decreases in the following order

28
Subjective

Despite their $-I$ effect, halogens are $o$ - and $p$-directing in haloarenes. Explain.

Explanation

Halogens have $(-I)$ and $(+R)$ effect, these groups are deactivating due to their $(-I)$ effect and they are ortho, para directing due to $(+R)$ effect.

29
Subjective

Why does presence of a nitro group make the benzene ring less reactive in comparison to the unsubstituted benzene ring. Explain.

Explanation

The meta - directing substituents (like $-\mathrm{NO}_2$ group) withdraw electrons from the benzene ring and thus, deactivate the benzene ring for further substitution and make the benzene ring less reactive in comparison to the unsubstituted benzene ring.